Fluorine-containing optically active composition for anti-infection

A compound and anti-infection technology, applied in anti-infective drugs, organic active ingredients, organic chemistry, etc., can solve the problems of no clinical application significance, high toxicity, and large irritation of racemic ulifloxacin, and achieve no skin and muscle Stimulation, low side effects, strong biological activity

Active Publication Date: 2009-10-07
GUANGZHOU PHARMACEUTICAL INDUSTRIAL RESEARCH INSTITUTE +1
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  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0010] The above literature fully demonstrates that racemic ulifloxacin is highly irritating and toxic, and has no clinical application significance

Method used

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  • Fluorine-containing optically active composition for anti-infection
  • Fluorine-containing optically active composition for anti-infection
  • Fluorine-containing optically active composition for anti-infection

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0028] Example 1, (S)-6-fluoro-1-methyl-4-oxo-(1-piperazinyl)-1H,4H-[1,3]thiazetidino[3,2 -a] the preparation of quinoline-3-carboxylic acid (abbreviation compound 2)

[0029] Dissolve 105 g of racemic ulifloxacin in 1500 mL of dimethyl sulfoxide, add dropwise a solution of 27 g of D-tartaric acid dissolved in 405 mL of dimethyl sulfoxide under stirring, turbidity and precipitation appear, and stir at room temperature for 20 hours , filtered, and the resulting solid was dried in vacuo to obtain 86 g. This solid was recrystallized and purified in dimethyl sulfoxide to obtain (S)-6-fluoro-1-methyl-4-oxo-(1-piper Azinyl)-1H, 4H-[1,3]thiazetidino[3,2-a]quinoline-3-carboxylic acid-D-tartrate 37 grams, elemental analysis C49.08%, H5.06%, N9.50%, S7.44% (molecular composition: C 16 h 16 FN 3 o 3 S.1 / 2C 4 h 6 o 6 .H 2 O, calculated value C48.86%, H4.78, N9.50%, S7.25%); add this salt into water to form a suspension, adjust the pH value to 7-8 with 2% NaOH aqueous solution und...

Embodiment 2

[0030] Example 2, (R)-6-fluoro-1-methyl-4-oxo-(1-piperazinyl)-1H,4H-[1,3]thiazetidine[3,2 -a] Preparation of quinoline-3-carboxylic acid (compound 3 for short) Dissolve 105 grams of racemic ulifloxacin in 1500 mL of dimethyl sulfoxide, add 27 grams of L-tartaric acid dropwise under stirring and dissolve in 405 mL di The solution of methyl sulfoxide appeared turbid and precipitated, stirred at room temperature for 20 hours, filtered, and the obtained solid was dried under vacuum to obtain 82 grams, and the solid was recrystallized and purified in dimethyl sulfoxide to obtain (R)- 6-fluoro-1-methyl-4-oxo-(1-piperazinyl)-1H,4H-[1,3]thiazetidino[3,2-a]quinoline-3- Carboxylic acid-L-tartrate 34 grams, add this salt into water to form a suspension, adjust the pH value to 7-8 with 2% NaOH aqueous solution under stirring, precipitate, filter and dry to obtain (R)-6-fluoro-1-methyl Base-4-oxo-(1-piperazinyl)-1H, 4H-[1,3]thiazetidino[3,2-a]quinoline-3-carboxylic acid 22 grams, specific...

Embodiment 3

[0031] Example 3 Lactic acid (S)-6-fluoro-1-methyl-4-oxo-(1-piperazinyl)-1H,4H-[1,3]thiazetidino[3,2 -a] the preparation of quinoline-3-carboxylic acid (abbreviated as compound 4)

[0032] At room temperature 20°C, add 30 mL of water to the reaction flask, add 1.6 g of lactic acid while stirring, and then add 5 g of (S)-6-fluoro-1-methyl-4-oxo-(1-piperazinyl)- 1H, 4H-[1,3]thiazetidino[3,2-a]quinoline-3-carboxylic acid, after stirring for 60 minutes, a substantially clear solution was obtained, which was decolorized by adding 5% activated carbon for 30 minutes and then filtered , the filtrate was added dropwise with 200 ml of absolute ethanol under stirring, and a solid precipitated at this time, continued to stir for 2 hours, filtered, the filter cake was crushed, and dried in vacuo at 50°C to obtain 3.6 grams of lactic acid (S)-6-fluoro-1-formazan Base-4-oxo-(1-piperazinyl)-1H,4H-[1,3]thiazetidino[3,2-a]quinoline-3-carboxylic acid, assay: [α ] D 20 =-116.5 (c=1.0, water);...

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Abstract

The invention relates to a fluorine-containing optically active composition for anti-infection, in particular to a quinolones optically active fluorine-containing composition anti-infective drug, i.e. a quinolones optically active fluorine-containing composition 1 showed by a right formula, wherein HA in the right formula is organic acid or inorganic acid which can form a composition accepted by pharmacology with (S)-6-fluorine-1-methyl-4-oxo-7-(1-piperazinyl)-1H and 4H-(1, 3) sulfur azetidine combined with (3, 2-a) quinoline-3-carboxylic acid. The quinolones optically active fluorine-containing composition 1 has stable property; compared with ulifloxacin, the quinolones optically active fluorine-containing composition 1 improves the water solubility and lowers the pH value of a water solution, is easy to dissolve in water and has higher biological activity, little renal toxicity and no skin and muscle irritation; the drug level of unobserved untoward effect is 30 mg / kg and is enhanced by 10 times comparing with the ulifloxacin, thus the quinolones optically active fluorine-containing composition 1 has low side effect and wide antimicrobial spectrum, and the activity of the quinolones optically active fluorine-containing composition 1 is 1-3 times higher than that of the racemic ulifloxacin.

Description

technical field [0001] The invention relates to a quinolone optically active fluorine-containing compound anti-infective drug, in particular to (S)-6-fluoro-1-methyl-4-oxo-7-(1-piperazinyl)-1H, 4H-[1,3]thiazetidino[3,2-a]quinoline-3-carboxylic acid forms pharmaceutically acceptable compounds with organic or inorganic acids. Background technique [0002] Infectious disease is the most common clinical disease, involving almost all clinical specialties, and it is also one of the most common causes of patient death. According to the World Health Organization report in 2000, the number of deaths from infectious diseases was as high as 33.3% of the total number of deaths from various causes. [0003] In the international market, quinolones account for about 18% of the market share of anti-infective drugs, with an average annual growth rate of 7%, and continue to grow at a high speed, ranking second only to β-lactam drugs in sales. Fluoroquinolones are also antibacterial drugs th...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D513/04A61K31/496A61K31/4743A61P31/00
CPCC07D513/04A61P31/00
Inventor 朱少璇陈矛刘学斌王玉平彭锋杨威曾琳玲冯伟成郑丽珍许淑文
Owner GUANGZHOU PHARMACEUTICAL INDUSTRIAL RESEARCH INSTITUTE
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